WO2019124332A1 - 粘着剤組成物、両面粘着シート及び積層体の製造方法 - Google Patents

粘着剤組成物、両面粘着シート及び積層体の製造方法 Download PDF

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Publication number
WO2019124332A1
WO2019124332A1 PCT/JP2018/046448 JP2018046448W WO2019124332A1 WO 2019124332 A1 WO2019124332 A1 WO 2019124332A1 JP 2018046448 W JP2018046448 W JP 2018046448W WO 2019124332 A1 WO2019124332 A1 WO 2019124332A1
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Prior art keywords
sensitive adhesive
pressure
meth
adhesive composition
mass
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PCT/JP2018/046448
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English (en)
French (fr)
Japanese (ja)
Inventor
隼介 塩田
万智 伊藤
滋呂 清水
竜也 大里
大輔 黒田
誠司 瀬口
錦織　義治
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王子ホールディングス株式会社
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Application filed by 王子ホールディングス株式会社 filed Critical 王子ホールディングス株式会社
Priority to KR1020207017335A priority Critical patent/KR102656758B1/ko
Priority to CN201880081790.7A priority patent/CN111492027B/zh
Priority to JP2019561089A priority patent/JPWO2019124332A1/ja
Publication of WO2019124332A1 publication Critical patent/WO2019124332A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/12—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers
    • C09J2301/124—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the arrangement of layers the adhesive layer being present on both sides of the carrier, e.g. double-sided adhesive tape
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition, a double-sided pressure-sensitive adhesive sheet, and a method of producing a laminate.
  • a display device such as a liquid crystal display (LCD) and a display device such as a touch panel
  • LCD liquid crystal display
  • a transparent double-sided adhesive sheet is used for the purpose of bonding optical members, and a transparent double-sided adhesive sheet is also used for bonding a display device and an input device. ing.
  • touch panels and liquid crystal displays described above include a component having a step caused by printing or the like.
  • a touch panel having a member subjected to frame-like printing is used.
  • the pressure-sensitive adhesive sheet is required to have a performance (adhesiveness) for bonding and fixing a member as well as a performance (step-following property) for filling a printing step.
  • patent document 1 it is a hot melt type adhesive sheet having the ability to easily follow a level difference by heating the pressure sensitive adhesive sheet, and the active energy ray is irradiated after the level difference is followed to cure the pressure sensitive adhesive sheet.
  • An after cure pressure-sensitive adhesive sheet has been proposed in which the tackiness is improved by doing this.
  • Touch panels and liquid crystal displays may be exposed to severe environments such as high temperature and high humidity. For this reason, there is a demand for a pressure-sensitive adhesive sheet in which the adhesion performance and the like do not change even in a severe environment such as high temperature and high humidity. That is, the pressure-sensitive adhesive sheet is also required to have durability in severe environments. However, in the conventional after-cure type pressure-sensitive adhesive sheet, there is a problem that when the durability is enhanced, the step following property is not sufficient.
  • the adhesive when attempting to improve the step following property, the adhesive may spread unintentionally at the time of bonding, and there was also a problem that the handling property at the time of bonding is inferior. .
  • the present inventors advanced examination for the purpose of providing the adhesive composition which has a level-difference followability and a handling property.
  • the glass transition temperature (Tg) of the main polymer is a hot melt type and after cure type pressure sensitive adhesive composition (pressure sensitive adhesive sheet).
  • Adhesive composition having both step followability and handling properties by setting the) to -50 ° C or higher, the main polymer weight average molecular weight to 300,000 to 450,000, and the thermal crosslinking agent content to a predetermined amount or less It was found that a thing (adhesive sheet) was obtained.
  • the present invention has the following configuration.
  • the content of the thermal crosslinking agent is less than 0.5 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer,
  • the adhesive composition whose gel fraction is 15.0% or less.
  • [3] A double-sided pressure-sensitive adhesive sheet obtained by converting the pressure-sensitive adhesive composition according to [1] or [2] into a sheet.
  • [4] A double-sided pressure-sensitive adhesive sheet with a release sheet comprising a release sheet on both sides of the double-sided pressure-sensitive adhesive sheet as described in [3].
  • a heat treatment is performed in a bonding process.
  • Step b A degassing step is included in a step after the bonding step, which is a step prior to the step of irradiating the active energy ray, and heat treatment is performed in the defoaming step.
  • [7] The method for producing a laminate according to [5] or [6], wherein the adherend is an optical member.
  • FIG. 1 is a cross-sectional view showing an example of the configuration of the release sheet-included double-sided pressure-sensitive adhesive sheet of the present invention.
  • FIG. 2 is a cross-sectional view showing an example of the configuration of the laminate.
  • the present invention relates to a photopolymerization initiator which initiates the polymerization reaction of a polyfunctional monomer by irradiation of active energy rays with 100 parts by mass of a (meth) acrylic copolymer, 0.1 to 10 parts by mass of a polyfunctional monomer.
  • the present invention relates to a pressure-sensitive adhesive composition containing 1 to 10 parts by mass.
  • the glass transition temperature (Tg) of the (meth) acrylic copolymer is ⁇ 50 ° C. or higher, and the weight average molecular weight is 300,000 to 450,000.
  • the content of the thermal crosslinking agent is less than 0.5 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer. Furthermore, the gel fraction of the pressure-sensitive adhesive composition of the present invention is 15.0% or less.
  • the pressure-sensitive adhesive composition of the present invention has the above-described constitution, it has both step followability and handling properties.
  • the pressure-sensitive adhesive composition of the present invention can also form a pressure-sensitive adhesive sheet having both step followability and handling properties.
  • the glass transition temperature and the weight average molecular weight of the (meth) acrylic copolymer which is the main polymer are in the predetermined ranges, and the content of the thermal crosslinking agent is in the predetermined ranges. , The step following ability and the handling ability can be enhanced.
  • the content of the thermal crosslinking agent is less than 0.5 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer, and the pressure-sensitive adhesive composition is a thermal crosslinking agent A configuration not containing
  • the aging step can be omitted when forming a pressure-sensitive adhesive sheet from the pressure-sensitive adhesive composition, and the time required for producing the pressure-sensitive adhesive sheet can be shortened. .
  • the pressure-sensitive adhesive composition of the present invention exhibits excellent step followability.
  • the pressure-sensitive adhesive composition of the present invention can follow the step without gaps even if there is a step having a height of 35 ⁇ m or more in the attached portion, for example, and in such a case, the step following property is excellent. Can be evaluated.
  • the pressure-sensitive adhesive composition of the present invention is also excellent in durability. Specifically, even when the pressure-sensitive adhesive composition of the present invention is treated in an environment of 85 ° C. and a relative humidity of 85% for 240 hours, no deterioration occurs and no generation of air bubbles or the like is observed.
  • the pressure-sensitive adhesive composition of the present invention is also excellent in handleability.
  • the handling property of the pressure-sensitive adhesive composition can be evaluated by the protrusion (Ooz value) of the pressure-sensitive adhesive at the time of bonding.
  • the pressure-sensitive adhesive composition of the present invention is a pressure-sensitive adhesive sheet having a thickness of 100 ⁇ m, the temperature of the press portion is set to 25 ° C., and the pressure-sensitive adhesive sheet spreads when pressed for 5 minutes at a pressure of 0.2 MPa.
  • (Ooz value) is small, it can be evaluated that the handling property is good.
  • the Worse value of the pressure-sensitive adhesive sheet is preferably 1.2 mm or less, more preferably 1.0 mm or less, and still more preferably 0.8 mm or less.
  • the Wooss value of an adhesive sheet is a value evaluated by the method as described in an Example.
  • the gel fraction of the pressure-sensitive adhesive composition of the present invention may be 15.0% or less, preferably 10.0% or less, more preferably 5.0% or less, and 4.0% or less Is more preferably 3.0% or less, still more preferably 2.0% or less. Further, the lower limit value of the gel fraction of the pressure-sensitive adhesive composition is not particularly limited, and may be, for example, 0%.
  • the gel fraction of the pressure-sensitive adhesive composition is preferably a gel fraction before the pressure-sensitive adhesive composition is completely cured by irradiation with active energy rays. By setting the gel fraction of the pressure-sensitive adhesive composition within the above range, it is possible to obtain a pressure-sensitive adhesive composition and a pressure-sensitive adhesive sheet excellent in level difference followability.
  • the gel fraction of the pressure-sensitive adhesive composition of the present invention is as described above, and the pressure-sensitive adhesive composition is in a semi-cured state.
  • being in a semi-cured state means that the pressure-sensitive adhesive composition has an active energy ray curing ability. That is, the pressure-sensitive adhesive composition of the present invention is a composition in a soft state before irradiation with active energy rays.
  • the gel fraction of the pressure-sensitive adhesive composition is preferably 60% or more, more preferably 65% or more, and preferably 70% or more. Is more preferred.
  • the gel fraction of the adhesive composition after active energy ray irradiation is measured, for example, after irradiating an active energy ray so that an accumulated light quantity may be 2000 mJ / cm ⁇ 2 > or more to an adhesive composition.
  • the integrated light quantity of the active energy ray is taken as the light quantity which can completely cure the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition of the present invention may be a sheet-like pressure-sensitive adhesive sheet as described later.
  • the pressure-sensitive adhesive composition of the present invention may be a gel-like pressure-sensitive adhesive composition, and may be, for example, a container-containing pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition of the present invention When using the pressure-sensitive adhesive composition of the present invention, it is preferable to include a heat treatment step when the pressure-sensitive adhesive composition is brought into contact with the adherend surface and / or after being brought into contact. And it is preferable to include the process of irradiating an active energy ray after a heat treatment process. That is, the pressure-sensitive adhesive composition of the present invention is a hot-melt type pressure-sensitive adhesive composition and an after-cure type pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition of the present invention contains a (meth) acrylic copolymer.
  • the (meth) acrylic copolymer is a main polymer contained in the pressure-sensitive adhesive composition, and such a polymer may be referred to as a base polymer.
  • the (meth) acrylic copolymer has a (meth) acrylic acid alkyl ester unit.
  • the "unit” is a repeating unit (monomer unit) constituting the polymer.
  • the (meth) acrylic acid alkyl ester unit is derived from the (meth) acrylic acid alkyl ester.
  • (meth) acrylic acid alkyl ester methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, (meth) Isobutyl acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate ( (Meth) acrylate isooctyl, (meth) acrylate n-nonyl, (meth) acrylate isononyl, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-undecyl (meth) acrylate, (meth
  • the (meth) acrylic copolymer may have another acrylic monomer unit other than the (meth) acrylic acid alkyl ester unit.
  • the acrylic monomer unit which has a crosslinkable functional group can be mentioned,
  • a hydroxyl group containing acrylic monomer unit, a glycidyl group containing acrylic monomer unit can be mentioned.
  • These monomer units may be used alone or in combination of two or more.
  • the hydroxy group-containing acrylic monomer unit is derived from the hydroxy group-containing acrylic monomer.
  • Examples of the hydroxy group-containing acrylic monomer include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate such as (meth) acrylate.
  • (meth) acrylic acid lactones such as (meth) acrylic acid [(mono, di or poly) alkylene glycols] such as alkyl (meth) acrylic acid mono (diethylene glycol) and (meth) acrylic acid monocaprolactone.
  • Examples of the glycidyl group-containing acrylic monomer unit include those derived from glycidyl group-containing acrylic monomers such as glycidyl (meth) acrylate.
  • the content of the other acrylic monomer unit is (meth) acrylic copolymer
  • the content is preferably 0.01 to 20% by mass, more preferably 0.5 to 10% by mass, based on the total mass of the polymer.
  • the content of the acrylic monomer unit having a crosslinkable functional group is preferably in the above range. If the content of the other acrylic monomer unit is equal to or more than the above lower limit value, the cohesion can be sufficiently increased, and if it is less than or equal to the above upper limit value, it becomes easy to secure sufficient adhesion.
  • the glass transition temperature (Tg) of the (meth) acrylic copolymer may be ⁇ 50 ° C. or higher, preferably ⁇ 49 ° C. or higher, and more preferably ⁇ 48 ° C. or higher. Further, the glass transition temperature (Tg) of the (meth) acrylic copolymer is preferably ⁇ 10 ° C. or less, more preferably ⁇ 20 ° C. or less, and still more preferably ⁇ 30 ° C. or less It is particularly preferable that the temperature is ⁇ 40 ° C. or less.
  • Tg glass transition temperature
  • the weight average molecular weight (Mw) of the (meth) acrylic copolymer may be from 300,000 to 450,000, preferably from 350,000 to 450,000, and more preferably from 360,000 to 430,000.
  • Mw weight average molecular weight
  • the step following can be achieved by setting the weight average molecular weight of the (meth) acrylic copolymer within the above range. It is easy to achieve both of the properties and durability.
  • the weight average molecular weight of the (meth) acrylic copolymer is a value determined by gel permeation chromatography (GPC) and calculated in terms of standard polystyrene.
  • the measurement conditions of gel permeation chromatography (GPC) are as follows.
  • Solvent Tetrahydrofuran column: Shodex KF801, KF803L, KF800L, KF800D (Showa Denko KK made four connection) Column temperature: 40 ° C Sample concentration: 0.5 mass% Detector: RI-2031 plus (made by JASCO) Pump: RI-2080plus (made by JASCO) Flow rate (flow rate): 0.8 ml / min Injection volume: 10 ⁇ l
  • a (meth) acrylic-type copolymer may use a commercially available thing, and may be manufactured by polymerizing an acryl monomer.
  • a commercially available product for example, OP-9200-1, OP-9200-3, OP-9200-4, OP-9200-5, OP-9200-7, etc. manufactured by Aika Kogyo Co., Ltd. can be used.
  • the polymerization method can be suitably selected from the polymerization method used normally.
  • a solution polymerization method, an emulsion polymerization method, a suspension polymerization method and the like can be mentioned.
  • the pressure-sensitive adhesive composition of the present invention contains a polyfunctional monomer.
  • the polyfunctional monomer is a monomer having two or more reactive double bonds in the molecule.
  • polyfunctional monomers examples include ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, and 1,4-di (meth) acrylic acid.
  • a commercial item can be used for a polyfunctional monomer.
  • Examples of commercially available products include ATM-4PL and A-TMM-3L manufactured by Shin-Nakamura Chemical Co., Ltd.
  • the pressure-sensitive adhesive composition may contain the polyfunctional monomer in an amount of 0.1 to 10 parts by mass, preferably 1 to 5 parts by mass, and preferably 2 to 4 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer. It is more preferable to contain part.
  • the above-mentioned polyfunctional monomers may be used alone or in combination of two or more. When two or more are used in combination, the total mass is preferably in the above range.
  • the pressure-sensitive adhesive composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator may be any as long as it can start the polymerization reaction of the above-mentioned polyfunctional monomer by irradiation of active energy rays.
  • active energy ray means an electromagnetic wave or charged particle beam having energy quantum, and includes ultraviolet light, electron beam, visible light, X-ray, ion beam and the like. Among them, ultraviolet rays or electron beams are preferable, and ultraviolet rays are particularly preferable, from the viewpoint of versatility.
  • Examples of the photopolymerization initiator include acetophenone initiators, benzoin ether initiators, benzophenone initiators, hydroxyalkylphenone initiators, thioxanthone initiators, and amine initiators.
  • acetophenone initiators include diethoxyacetophenone, benzyl dimethyl ketal and the like.
  • Specific examples of the benzoin ether initiator include benzoin and benzoin methyl ether.
  • Specific examples of benzophenone initiators include benzophenone and methyl o-benzoylbenzoate.
  • hydroxyalkyl phenone initiator examples include 1-hydroxy-cyclohexyl-phenyl-ketone and the like.
  • thioxanthone initiators include 2-isopropyl thioxanthone, 2,4-dimethyl thioxanthone and the like.
  • amine initiator examples include triethanolamine and ethyl 4-dimethylbenzoate.
  • a commercial item can be used for a photoinitiator.
  • Examples of commercially available products include TZT and Omnirad 184 manufactured by IGM Resin.
  • the pressure-sensitive adhesive composition may contain 0.1 to 10 parts by mass of a photopolymerization initiator with respect to 100 parts by mass of the (meth) acrylic copolymer, and preferably 0.1 to 3 parts by mass.
  • the photopolymerization initiators may be used alone or in combination of two or more. When two or more are used in combination, the total mass is preferably in the above range.
  • the content of the thermal crosslinking agent in the pressure-sensitive adhesive composition of the present invention is less than 0.5 parts by mass and not more than 0.3 parts by mass with respect to 100 parts by mass of the (meth) acrylic copolymer.
  • the amount is preferably 0.2 parts by mass or less, and more preferably 0.1 parts by mass or less.
  • the content of the thermal crosslinking agent is particularly preferably 0 parts by mass.
  • the adhesive composition of this invention is an aspect which does not contain a thermal crosslinking agent substantially, In such a case, when forming an adhesive sheet from an adhesive composition, an aging process may be skipped. It is possible to reduce the time required for producing the pressure-sensitive adhesive sheet.
  • thermal crosslinking agents include, for example, isocyanate compounds, epoxy compounds, oxazoline compounds, aziridine compounds, metal chelate compounds, butylated melamine compounds, etc. And a thermal crosslinker of Among these, isocyanate compounds and epoxy compounds are preferably used.
  • the thermal crosslinking agent is selected in consideration of the reactivity with the crosslinkable functional group possessed by the (meth) acrylic copolymer. For example, when the (meth) acrylic copolymer contains a hydroxy group as a crosslinkable functional group, it is preferable to use an isocyanate compound in view of the reactivity of the hydroxy group.
  • One type of thermal crosslinking agent may be used alone, or two or more types may be used in combination.
  • isocyanate compound examples include tolylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate and the like.
  • an epoxy compound for example, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, glycerin diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol di Glycidyl ether, tetraglycidyl xylene diamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, trimethylolpropane polyglycidyl ether, diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, sorbitol polyglycid
  • polyfunctional acrylates such as polyethylene glycol diacrylate, neopentyl glycol diacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,6-hexanediol diacrylate, 1,9 Nonanediol diacrylate, trimethylolpropane triacrylate, pentaerythritol (tri / tetra) acrylate, etc. may be used.
  • the pressure-sensitive adhesive composition of the present invention may contain a solvent.
  • the solvent is used to improve the coating suitability of the pressure-sensitive adhesive composition.
  • Such solvents include, for example, hydrocarbons such as hexane, heptane, octane, toluene, xylene, ethylbenzene, cyclohexane and methylcyclohexane; halogenated hydrocarbons such as dichloromethane, trichloroethane, trichloroethylene, tetrachloroethylene and dichloropropane; methanol Alcohols such as ethanol, propanol, isopropyl alcohol, butanol, isobutyl alcohol, diacetone alcohol; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran etc.
  • hydrocarbons such as hexane, heptane, octane, toluene, xylene, ethylbenzene, cyclohexane and methylcyclohexane
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone etc Methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, amyl acetate, ethyl butyrate etc.
  • Ester ethers ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, polyols and derivatives thereof such as propylene glycol monomethyl ether acetate.
  • One solvent may be used alone, or two or more solvents may be used in combination.
  • the content of the solvent contained in the pressure-sensitive adhesive composition is preferably 80% by mass or less, more preferably 50% by mass or less, based on the total mass of the pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive composition of the present invention may contain other components other than the above as long as the effects of the present invention are not impaired.
  • components known as additives for pressure-sensitive adhesives can be mentioned.
  • it can be selected as required from light stabilizers such as plasticizers, antioxidants, metal corrosion inhibitors, tackifiers, silane coupling agents, ultraviolet absorbers and hindered amine compounds.
  • a nonfunctional acrylic polymer can be used as a plasticizer.
  • a nonfunctional acrylic polymer is a polymer consisting only of an acrylic monomer unit having no functional group other than an acrylate group, or an acrylic monomer unit having no functional group other than an acrylate group and a functional group It means a polymer composed of non-acrylic monomer units not having.
  • an acryl-type monomer unit which does not have functional groups other than an acrylate group the thing similar to a non-crosslinkable (meth) acrylic acid ester unit is mentioned, for example.
  • non-acrylic monomer units having no functional group examples include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl caproate, vinyl caprylate, vinyl caprate, vinyl caprate, vinyl laurate, vinyl myristate, vinyl palmitate, Examples thereof include vinyl stearates, vinyl cyclohexanecarboxylates, vinyl esters of carboxylic acids such as vinyl benzoate, and styrene.
  • antioxidants examples include phenol based antioxidants, amine based antioxidants, lactone based antioxidants, phosphorus based antioxidants, sulfur based antioxidants and the like. One of these antioxidants may be used alone, or two or more thereof may be used in combination.
  • benzotriazole resin can be mentioned.
  • tackifiers include rosin resins, terpene resins, terpene phenol resins, coumarone indene resins, styrene resins, xylene resins, phenol resins, petroleum resins and the like.
  • silane coupling agent a mercapto type silane coupling agent, a (meth) acrylic type silane coupling agent, an isocyanate type silane coupling agent, an epoxy type silane coupling agent, an amino type silane coupling agent etc. are mentioned, for example .
  • UV absorber include benzotriazole compounds and benzophenone compounds.
  • the present invention also relates to a double-sided pressure-sensitive adhesive sheet in which the above-described pressure-sensitive adhesive composition is formed into a sheet.
  • the double-sided pressure-sensitive adhesive sheet of the present invention may be a double-sided pressure-sensitive adhesive sheet made of a pressure-sensitive adhesive composition, or may be a double-sided pressure-sensitive adhesive sheet obtained by semi-curing the pressure-sensitive adhesive composition by heat or active energy rays. Good.
  • the gel fraction of the double-sided pressure-sensitive adhesive sheet of the present invention is preferably 15.0% or less, more preferably 10.0% or less, still more preferably 5.0% or less, and 4.0% The content is more preferably the following, still more preferably 3.0% or less, and particularly preferably 2.0% or less.
  • FIG. 1 is a schematic view showing a cross section of an example of the double-sided pressure-sensitive adhesive sheet of the present invention.
  • the double-sided pressure-sensitive adhesive sheet 11 may be a double-sided pressure-sensitive adhesive sheet 1 provided with a release sheet 12a and a release sheet 12b on both sides thereof.
  • the double-sided pressure-sensitive adhesive sheet 11 may be a single-layer double-sided pressure-sensitive adhesive sheet as shown in FIG. 1 or may be a multilayer double-sided pressure-sensitive adhesive sheet in which a plurality of pressure-sensitive adhesive layers are laminated.
  • the double-sided pressure-sensitive adhesive sheet 11 may be a double-sided pressure-sensitive adhesive sheet provided with a pressure-sensitive adhesive layer on both sides of a substrate (preferably, a transparent substrate).
  • the surface of the double-sided pressure-sensitive adhesive sheet 11 is preferably covered with a release sheet 12a and a release sheet 12b.
  • a release sheet a peelable laminate sheet having a release sheet substrate and a release agent layer provided on one side of the release sheet substrate, or a polyolefin film such as a polyethylene film or a polypropylene film as a low polarity substratecan be mentioned.
  • Papers and polymer films are used for the release sheet base in the release laminate sheet.
  • a general-purpose addition type or condensation type silicone release agent or a long chain alkyl group-containing compound is used as the release agent constituting the release agent layer.
  • an addition-type silicone release agent having high reactivity is preferably used.
  • Specific examples of silicone release agents include BY24-4527 and SD-7220 manufactured by Toray Dow Corning Silicone Co., Ltd., KS-3600 manufactured by Shin-Etsu Chemical Co., Ltd., KS-774 and X62-2600, etc. Can be mentioned.
  • a silicone resin which is an organic silicon compound having a SiO 2 unit and a (CH 3 ) 3 SiO 1/2 unit or a CH 2 CHCH (CH 3 ) SiO 1/2 unit in a silicone-based release agent preferable.
  • Specific examples of the silicone resin include BY24-843, SD-7292, SHR-1404, etc. manufactured by Toray Dow Corning Silicone Co., Ltd., and KS-3800, X92-183, etc. manufactured by Shin-Etsu Chemical Co., Ltd.
  • a commercial item may be used as the peelable laminated sheet.
  • a heavy separator film which is a release-treated polyethylene terephthalate film manufactured by Teijin DuPont Films Ltd.
  • a light separator film which is a release-treated polyethylene terephthalate film manufactured by Teijin DuPont Films Ltd. it can.
  • the pressure-sensitive adhesive sheet of the present invention preferably has a pair of release sheets having different release forces. That is, in order to make it easy to peel off the release sheet, it is preferable that the release properties of the release sheet 12a and the release sheet 12b be different. When the releasability from one side and the releasability from the other are different, it becomes easy to peel off only the release sheet having the higher releasability first. In that case, the releasability of the release sheet 12a and the release sheet 12b may be adjusted according to the bonding method and the bonding order.
  • the thickness of the pressure-sensitive adhesive sheet of the present invention is preferably 5 to 500 ⁇ m, more preferably 30 to 300 ⁇ m, and still more preferably 50 to 200 ⁇ m.
  • the pressure-sensitive adhesive composition of the present invention When using the pressure-sensitive adhesive composition of the present invention, the pressure-sensitive adhesive composition is brought into contact with the adherend surface. When the pressure-sensitive adhesive composition is brought into contact with the adherend surface and / or after being brought into contact, it is preferable to include a heat treatment step. Then, after the heat treatment step, a step of irradiating an active energy ray is included. Thus, a laminate is obtained. That is, the method for producing a laminate of the present invention includes a bonding step of bringing a pressure-sensitive adhesive composition into contact with the surface of an adherend, and a step of irradiating an active energy ray; And / or process step). (A process) A heat treatment is performed in a bonding process. (Step b) A degassing step is included in a step after the bonding step, which is a step prior to the step of irradiating the active energy ray, and heat treatment is performed in the defoaming step.
  • the pressure-sensitive adhesive composition of the present invention may be a double-sided pressure-sensitive adhesive sheet made of a pressure-sensitive adhesive composition, and is a double-sided pressure-sensitive adhesive sheet obtained by semi-curing the pressure-sensitive adhesive composition by heat or active energy rays. It is also good.
  • the method for producing a laminate includes a bonding step of bringing a double-sided pressure-sensitive adhesive sheet into contact with the adherend surface, and a step of irradiating an active energy ray, and at least the steps (a) and (b) It may be one including any.
  • the pressure-sensitive adhesive composition or the double-sided pressure-sensitive adhesive sheet is bonded to an adherend.
  • a bonding method the roll bonding method, the vacuum bonding method, etc. can be mentioned, for example.
  • the heat treatment is preferably performed at 40 to 59.degree.
  • the heating temperature is also preferably 50 to 59.degree.
  • the treatment temperature at the time of performing the heat treatment in the bonding step and / or the subsequent step of the bonding step can be suppressed lower than usual, and even in such a case Therefore, the risk of damaging the adherend can be extremely low.
  • the photothermal cost at the time of manufacturing a laminated body can be suppressed, and the manufacturing efficiency of a laminated body can also be raised more effectively.
  • the heat treatment at 40 to 59 ° C. is preferably performed in the bonding step or in the defoaming step.
  • heat processing may be performed in both processes of a bonding process and a defoaming process.
  • a bonding process a roll bonding process and a vacuum bonding process can be mentioned, for example.
  • a degassing process an autoclave process can be mentioned, for example. That is, the heat treatment at 40 to 59 ° C. is preferably performed in at least one process selected from an autoclave treatment process, a roll bonding process and a vacuum bonding process.
  • the heating setting temperature in the autoclave treatment step, the roll bonding step and the vacuum bonding step is preferably 40 to 59 ° C.
  • an active energy ray is irradiated to the adhesion thing of an adhesive composition or a double-sided adhesive sheet, and a to-be-adhered body.
  • the step of irradiating the active energy ray can also be called a post-curing step.
  • an ultraviolet ray, an electron beam, a visible ray, an X ray, an ion beam etc. are mentioned, According to the photoinitiator contained in an adhesive layer, it can select suitably. Among them, ultraviolet rays or electron beams are preferable, and ultraviolet rays are particularly preferable, from the viewpoint of versatility.
  • a light source of ultraviolet light for example, a high pressure mercury lamp, low pressure mercury lamp, ultra high pressure mercury lamp, metal halide lamp, carbon arc, xenon arc, electrodeless ultraviolet lamp and the like can be used.
  • the electron beam for example, electron beams emitted from various types of electron beam accelerators such as Cockloft Wald type, Bandeklav type, resonant transformer type, insulating core transformer type, linear type, dynamitron type, high frequency type and the like are used it can.
  • Radiation output of the UV light it is preferable that the integrated quantity of light is made to be a 100 ⁇ 10000mJ / cm 2, and more preferably made to be 500 ⁇ 5000mJ / cm 2.
  • the laminate produced by the above-described production method comprises a post-cured pressure-sensitive adhesive composition (double-sided pressure-sensitive adhesive sheet) and an adherend.
  • the laminate of the present invention preferably has an adherend on both sides of the post-cured pressure-sensitive adhesive composition (double-sided pressure-sensitive adhesive sheet).
  • the pressure-sensitive adhesive composition (double-sided pressure-sensitive adhesive sheet) of the present invention is preferably used for bonding an adherend having a stepped portion.
  • FIG. 2 is a cross-sectional view showing an example of the configuration of a laminate 30 in which the double-sided pressure-sensitive adhesive sheet 11 of the present invention is bonded to an adherend 31 having a step portion 32.
  • the adherend 31 has a stepped portion 32.
  • the thickness of the step portion 32 can be 5 to 60 ⁇ m.
  • the double-sided adhesive sheet 11 of this invention can be used for the bonding of the to-be-adhered body which has a level
  • the double-sided pressure-sensitive adhesive sheet 11 of the present invention can also be used for bonding an adherend having a thickness of the step portion 32 of 35 ⁇ m or more.
  • the adherend 31 is preferably an optical member.
  • an optical member each structural member in optical products, such as a touch panel and an image display device, can be mentioned.
  • an ITO film in which an ITO film is provided on a transparent resin film an ITO glass in which an ITO film is provided on the surface of a glass plate, a transparent conductive film obtained by coating a conductive polymer on a transparent resin film Hard coat films, fingerprint resistant films and the like can be mentioned.
  • the double-sided pressure-sensitive adhesive sheet of the present invention is preferably for sensor lamination of a touch panel, and more preferably for sensor lamination of a touch panel using a touch pen.
  • an ITO film in which an ITO film is provided on a transparent resin film an ITO glass in which an ITO film is provided on the surface of a glass plate, and a conductive resin Polymer-coated transparent conductive films are preferred.
  • the antireflection film used for a liquid crystal display device an orientation film, a polarizing film, retardation film, a brightness improvement film etc. are mentioned, for example.
  • materials used for these members include glass, polycarbonate, polyethylene terephthalate, polymethyl methacrylate, polyethylene naphthalate, cycloolefin polymer, triacetyl cellulose, polyimide, and cellulose acylate.
  • Example 1 Preparation of pressure-sensitive adhesive composition
  • 100 parts by mass of (meth) acrylic copolymer manufactured by Aika Kogyo Co., Ltd .: OP-9200-3
  • 3 parts by mass of polyfunctional monomer manufactured by Shin-Nakamura Chemical Co., Ltd .: ATM-4PL
  • photopolymerization initiator IGM Resins Co., Ltd.
  • Product 1.5 parts by mass of TZT was mixed, and stirred for 3 minutes under atmospheric pressure using a stirrer (SHASHIN KAGAKU: SK-200 TVS) to prepare a pressure-sensitive adhesive composition.
  • SHASHIN KAGAKU SK-200 TVS
  • a 38 ⁇ m-thick polyethylene terephthalate film (first release sheet) (a release sheet manufactured by Oji F-TEX, Inc .: 38RL-07) provided with a release agent layer treated with a silicone-based release agent, with the pressure-sensitive adhesive composition prepared as described above
  • the surface of (2) was uniformly coated with an applicator so that the coated film thickness after drying was 100 ⁇ m. Then, it dried in 100 degreeC of air circulation type thermostatic ovens for 3 minutes, and formed the adhesive layer on the surface of a 1st peeling sheet.
  • a second release sheet (manufactured by Oji F-TEX Co., Ltd .: 38RL-07 (L)) having a thickness of 38 ⁇ m is attached to the surface of the pressure-sensitive adhesive layer to form a pair of pressure-sensitive adhesive layers having a difference in release force.
  • a UV curable ink was screen printed on the surface of a glass plate (90 mm long ⁇ 50 mm wide ⁇ 0.5 mm thick) in a frame shape (90 mm long ⁇ 50 mm wide, 5 mm wide) so that the coating thickness would be 5 ⁇ m.
  • ultraviolet rays were irradiated to cure the printed ultraviolet curable ink. This process was repeated a predetermined number of times to obtain a printed stepped glass having a stepped portion with a predetermined thickness described in Tables 1 to 3.
  • the double-sided pressure-sensitive adhesive sheet with a release sheet obtained above is cut into a shape of 90 mm long ⁇ 50 mm wide, the first release sheet is peeled off, and a pressure-sensitive adhesive is used using a laminator (manufactured by Eubon Co., Ltd., IKO-650 EMT) A layer was pasted so that the frame-like printing whole surface of printing level difference glass might be covered. Thereafter, the second release sheet is peeled off, and a glass plate (90 mm long ⁇ 50 mm wide ⁇ 0.5 mm thick) is bonded to the surface of the exposed pressure-sensitive adhesive layer with the above laminator, and defoaming treatment (autoclave treatment: 40 ° C, 0.5 MPa, 10 minutes) was performed.
  • autoclave treatment 40 ° C, 0.5 MPa, 10 minutes
  • ultraviolet rays were irradiated from the side of the printing step glass with an ultraviolet irradiator (manufactured by Eye Graphics Co., Ltd., ECS-301G1) so as to obtain the integrated light amount described in Tables 1 to 3, to obtain a laminate.
  • an ultraviolet irradiator manufactured by Eye Graphics Co., Ltd., ECS-301G1
  • Example 2 When bonding a glass plate (90 mm in length ⁇ 50 mm in width ⁇ 0.5 mm in thickness) to the surface of the pressure-sensitive adhesive layer on the side of the second release sheet in (the method for producing a laminate) in Example 1; A laminate was obtained in the same manner as in Example 1 except that lamination was carried out in a heated state at ° C. and then defoaming treatment (autoclave treatment: 40 ° C., 0.5 MPa, 10 minutes) was not performed.
  • autoclave treatment 40 ° C., 0.5 MPa, 10 minutes
  • Example 3 When bonding a glass plate (90 mm in length ⁇ 50 mm in width ⁇ 0.5 mm in thickness) to the surface of the pressure-sensitive adhesive layer on the side of the second release sheet in (the method for producing a laminate) in Example 1; A laminate was obtained in the same manner as Example 1, except that the lamination was carried out in the heated state at ° C.
  • Example 4 A glass plate (90 mm in length) was formed on the surface of the pressure-sensitive adhesive layer exposed by using a vacuum bonding machine (manufactured by Joyo Engineering Co., Ltd .: vacuum laminating apparatus (JE2020B-MVH)) in (Production method of laminate) of Example 1 ⁇ 50 mm ⁇ 0.5 mm thickness 40 ° C, weak pressure 0.6 kN, strong pressure 1.2 kN, vacuum pressure 100 Pa, pressure holding time 10 s, degassing treatment (autoclave treatment: 40 ° C., A laminate was obtained in the same manner as Example 1 except that 0.5 MPa for 10 minutes was not performed.
  • a vacuum bonding machine manufactured by Joyo Engineering Co., Ltd .: vacuum laminating apparatus (JE2020B-MVH)
  • JE2020B-MVH vacuum laminating apparatus
  • Example 5 A glass plate (90 mm long ⁇ 50 mm wide ⁇ 0.5 mm thick) was bonded at 40 ° C. to the surface of the pressure-sensitive adhesive layer exposed using a vacuum bonding machine in (Production method of laminate) of Example 1 A laminate was obtained in the same manner as Example 1 except for the above.
  • Example 6 A laminate was obtained in the same manner as in Example 1 except that the autoclave treatment temperature was changed to 55 ° C. in (Production method of laminate) of Example 1.
  • Example 7 A laminate was obtained in the same manner as in Example 1 except that the autoclave treatment temperature was changed to 59 ° C. in (Production method of laminate) of Example 1.
  • Example 8 A laminate was obtained in the same manner as in Example 1 except that the autoclave treatment temperature was changed to 55 ° C., and the time was changed to 30 minutes in (Production method of laminate) of Example 1.
  • Example 9 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-1 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Example 10 The (meth) acrylic copolymer was changed to OP-9200-1 (manufactured by Aika Kogyo Co., Ltd.) in (preparation of a pressure-sensitive adhesive composition) in Example 1 and the temperature of autoclave treatment was used in (a method of preparing a laminate) A laminate was obtained in the same manner as in Example 1 except that 55.degree. C. was changed.
  • Example 11 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-5 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Example 12 The (meth) acrylic copolymer was changed to OP-9200-5 (manufactured by Aika Kogyo Co., Ltd.) in (preparation of a pressure-sensitive adhesive composition) in Example 1 and the temperature of autoclave treatment was used in (a method of preparing a laminate) A laminate was obtained in the same manner as in Example 1 except that 55.degree. C. was changed.
  • Example 13 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-7 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Example 14 The (meth) acrylic copolymer is changed to OP-9200-7 (manufactured by Aika Kogyo Co., Ltd.) in (preparation of a pressure-sensitive adhesive composition) in Example 1 (a method of preparing a laminate), which is an autoclave.
  • a laminate was obtained in the same manner as in Example 1 except that the treatment temperature was changed to 55 ° C.
  • Example 15 In Example 1 (preparation of a pressure-sensitive adhesive composition), 0.3 part by mass of a thermal crosslinking agent (manufactured by Tosoh Corporation: Coronate L-55E) is added with respect to 100 parts by mass of a (meth) acrylic copolymer.
  • a laminate was obtained in the same manner as in Example 1 except that the pressure-sensitive adhesive sheet was aged at 23 ⁇ 5 ° C. and 50 ⁇ 10% relative humidity for 7 days at the end of the process of (preparation of pressure-sensitive adhesive sheet).
  • Example 16 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-4 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Example 1 In (Preparation of pressure-sensitive adhesive composition) of Example 1, a thermal crosslinking agent (manufactured by Tosoh Corp .: Coronate L-55E) is added in an amount of 1.0 part by mass with respect to 100 parts by mass of the (meth) acrylic copolymer. A laminate was obtained in the same manner as in Example 1 except that the pressure-sensitive adhesive sheet was aged at 23 ⁇ 5 ° C. and 50 ⁇ 10% relative humidity for 7 days at the end of the process of (preparation of pressure-sensitive adhesive sheet).
  • a thermal crosslinking agent manufactured by Tosoh Corp .: Coronate L-55E
  • Comparative Example 2 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-6 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Comparative Example 3 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-8 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Comparative Example 4 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-9200-9 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • Comparative Example 5 A laminate was prepared in the same manner as in Example 1 except that (meth) acrylic copolymer was changed to OP-7000-V6 (manufactured by Aika Kogyo Co., Ltd.) in (Preparation of pressure-sensitive adhesive composition) in Example 1. Obtained.
  • ⁇ Durability> The laminate was placed in an environment of 85 ° C. and relative humidity of 85% for 240 hours, and observed for no bubbles in the entire sample with a microscope (magnification: 25 times) and evaluated based on the following criteria. ⁇ : There is no generation of air bubbles at all. X: Air bubbles are generated.
  • a sheet piece was cut out in a size of 30 mm long ⁇ 30 mm wide from the double-sided pressure-sensitive adhesive sheet with a release sheet.
  • One side of the release sheet of the sheet piece was peeled off, and the pressure-sensitive adhesive layer peeled off was attached to the silicone-treated side of a release sheet (A71 100 ⁇ m: Teijin DuPont film) cut out in advance to 50 mm square.
  • the silicone-treated side of a release sheet (A38 # 50: Teijin DuPont film) which had been separately cut into 50 mm squares was placed on the other release sheet remaining on the sheet piece.
  • the weight average molecular weight of the (meth) acrylic copolymer is 300,000 to 450,000
  • the Tg of the (meth) acrylic copolymer is -50 ° C. or higher
  • the heat crosslinks It was found that when the additive amount of the agent is less than 0.5 parts by mass, level difference followability and good handling characteristics can be obtained.
  • Example 15 which added 0.3 mass part of thermal crosslinking agents with respect to the (meth) acrylic-type copolymer, although aging was required, the characteristic of level
  • Comparative Example 1 the thermal crosslinking agent was added in an amount of 1.0 part by mass with respect to the (meth) acrylic copolymer, so that the step followability was inferior.
  • Comparative Example 3 has a large molecular weight of the (meth) acrylic copolymer
  • Comparative Example 4 has a small molecular weight of the (meth) acrylic copolymer, but the Tg of the (meth) acrylic copolymer is high. As a result, the step followability was poor.
  • the Tg of the (meth) acrylic copolymer is low in Comparative Example 2, and the Tg of the (meth) acrylic copolymer is low in Comparative Example 5 and the molecular weight of the (meth) acrylic copolymer is small. The result was poor handling.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
PCT/JP2018/046448 2017-12-18 2018-12-18 粘着剤組成物、両面粘着シート及び積層体の製造方法 WO2019124332A1 (ja)

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JP2017173479A (ja) * 2016-03-23 2017-09-28 三菱ケミカル株式会社 画像表示装置構成用積層体及び画像表示装置の製造方法

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WO2020250887A1 (ja) * 2019-06-12 2020-12-17 王子ホールディングス株式会社 粘着シート及び積層体

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